Potassium Carbonate → HCID 59322207, compound

HRID 2060255Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([O:24][C:25]([C:27]1([CH2:41]I)[CH2:31][CH2:30][N:29]([C:32](=[O:40])[C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[CH2:28]1)=[O:26])[CH3:23]>CN(C)C=O>[CH2:22]([O:24][C:25]([C:27]1([CH2:41][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)[CH2:31][CH2:30][N:29]([C:32](=[O:40])[C:33]2[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=2)[CH2:28]1)=[O:26])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

4′-Hydroxy-4-biphenyl carbonitrile (329 mg, 1.68 mmol) and potassium carbonate (317 mg, 2.30 mmol) were added to a stirred solution of 1-(4-fluoro-benzoyl)-3-iodomethyl-pyrrolidine-3-carboxylic acid ethyl ester (620 mg, 1.53 mmol) (see Preparation 12) in dimethylformamide (7 mL). The reaction mixture was heated at 80° C. for 18 hours then partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was washed with water (2000 mL), dried over magnesium sulfate then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with 3:1→1:1 heptane:EtOAc to afford the title compound as a white solid (517 mg, 71%).

Workup

customthen partitioned between ethyl acetate (100 mL) and water (100 mL)
washThe organic layer was washed with water (2000 mL)
dry with materialdried over magnesium sulfate
concentrationthen concentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel
washeluting with 3:1→1:1 heptane

Sources & evidence

ORD record: ord-90c7838baa954403a6e75ff920d5bd34
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278343B2

Reaction notes

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